Princess Diana’s beauty evolution, from fresh-faced ingenue to royal icon

As the world commemorates the 25th anniversary of Princess Diana’s tragic death, we look back at her best beauty moments—and the haircut that confirmed her place as an icon

By Celia Ellenberg

2 September 2022

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Ahead of the 25th anniversary of Princess Diana’s untimely death today, there has been a flurry of series, films, and documentaries dedicated to the life and legacy of Lady Spencer, from the most recent season of The Crown to the Spencer biopic starring Kristen Stewart.

The latest account of Diana’s life, a new documentary from HBO called The Princess, tells the story of her life and death through highly-curated archival footage, painting an intimate and eye-opening portrait. It highlights that with a candid manner and human touch that earned her the nickname the People’s Princess, Diana’s strength and struggles often played out in the public eye. So, too, did her fashion progression—from her early, girlish leanings, to her decade-appropriate experiments with ’80s-era hair feathering, and teased-up volume topped off with colorful headpieces, jeweled accessories, and bold makeup. But it was in 1990 that she really came into her own after a fortuitous encounter with the hairstylist Sam McKnight on the set of a British Vogue shoot.

As the oft-told story goes, McKnight had used a few editorial tricks to make Diana’s hair appear smaller and shorter for the photos; it looked great, so he suggested she cut it. “She said, ‘Shall we do it now?’ So I did. It was simple as that,” recalls McKnight. “The ’80s were gone, and she was—bang!—in the ’90s.” A newfound ability to further tweak the minimal, no-fuss style on her own—tucking it behind her ears, adding bangs, wearing it sleek or soft—became indicative of Diana’s personal evolution into what McKnight describes as “a streamlined ’90s working princess” who radiated confidence.

McKnight would go on to work with Diana until her death, often seeing her once or twice a day and helping to craft some of her most iconic beauty moments, from the cut heard round the world, to the wet look he gave her for the 1995 CFDA awards, where she was a celebrity presenter. “We had so much fun and a lot of laughter for seven years,” says McKnight. “I miss her still.” Here, a look back at some of the Princess of Wales’s most memorable beauty moments.